2-Bromopyridine → 6'-Methoxy-2,3'-bipyridyl

Participants

Reaction Conditions

Reaction Steps

In a 300 mL inner volume flask replaced by nitrogen, tetrahydrofuran solution of isopropylmagnesium chloride (19.5% by weight, 30.3 g, 57.5 mmol) was charged, and cooled at 10° C., and then tetrahydrofuran solution (20 g) of 5-bromo-2-methoxypyridine (9.4 g, 50.0 mmol) was added dropwise in the range of 10 to 20° C. for 1.0 hour. After adding dropwise, the reaction mixture was stirred in the range of 10 to 20° C. for 1.5 hours, and then added dropwise to the tetrahydrofuran solution (20 g) containing 2-bromopyridine (7.9 g, 50.0 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.14 g, 0.25 mmol) in the range of 10 to 20° C. for 2.0 hours. After adding dropwise, the reaction mixture was stirred in the range of 10 to 20° C. for 4.0 hours, however, 6-methoxy-3,2′-bipyridine could not be obtained.

Provenance & Evidence